Acetic Acid → HCID 86736643, compound

HRID 1863193Notes

Reaction equation

HRID 1863193 reaction equation
[CH3:1][P:2]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C([N-]C(C)C)(C)C.[Li+].[C:25]1([CH2:31]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(=O)C>O1CCCC1.CCOCC>[C:6]1([CH2:5][O:4][P:2]([CH2:12][C:13]([O:15][CH3:16])=[O:14])([CH2:1][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:3])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7498Benzyl BromideHCID 2724682Lithium diisopropylamideHCID 86736642HCID 86736642, compound

Product 1

HCID 86736643HCID 86736643, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of [methyl(phenylmethoxy)phosphinyl]acetic acid, methyl ester (1.0 gm., 0.004 mole) in 20 ml. of tetrahydrofuran is added over 50 minutes to a solution of lithium diisopropylamide (0.008 mol.) in tetrahydrofuran maintained at -78° under argon. Following the addition, stirring is continued at -78° for 20 minutes. Phenylmethyl bromide (0.684 gm., 0.004 mol.) in tetrahydrofuran (5 ml.) is then added and the mixture is stirred for 2 hours at -78° and for one hour at 0°. The mixture is then neutralized to pH5 with acetic acid and poured into ether. The ether layer is washed with water, 5% potassium bisulfate and brine, and dried over magnesium sulfate. Evaporation in vacuo yields a residue which is chromatographed on silica gel with dichloromethane/ethyl acetate. The product, [(2-phenylethyl)(phenylmethoxy)phosphinyl] acetic acid, methyl ester (0.66 gm., 50%) is identical by TLC and NMR to that prepared in Example 6.

Workup

  1. temperaturemaintained at -78° under argon
  2. additionthe addition
  3. stirringthe mixture is stirred for 2 hours at -78° and for one hour at 0°
  4. washThe ether layer is washed with water, 5% potassium bisulfate and brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation in vacuo
  7. customyields a residue which
  8. customis chromatographed on silica gel with dichloromethane/ethyl acetate
  9. customthat prepared in Example 6

Sources & evidence

ORD record
ord-868512b6976f45a48df579355707b1e0
Source dataset
uspto-grants-1979_09
Patent number
US04168267

Reaction notes

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